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Pittsfield, MA accommodations
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288 Lodgings in Pittsfield, MA

Search Lodgings near the Old Town in Pittsfield, MA

Choosing central accommodation in downtown Pittsfield, MA maximizes your time, putting popular museums, historic districts, and local restaurants within walking distance.

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield - Pittsfield, MA
10 1 review

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield

apartment, Pittsfield
This Pittsfield apartment is located near Tanglewood Music Center, Colonial Theater, Herman Melville's Arrowhead, and Hancock Shaker Village.
This one-bedroom, one-bathroom unit accommodates up to four guests and features a king bed, a sofa bed, air conditioning, and internet.
Downtown Apartment A - Pittsfield, MA
9.9 107 reviews

Downtown Apartment A

apartment, Pittsfield
This Pittsfield apartment is conveniently located in a quiet neighborhood, just 5 minutes from Bousquet Ski Area and close to Jimmy Peak, making it ideal for winter sports enthusiasts. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment is a 2-bedroom rental that can accommodate up to 4 guests. It features a full kitchen with a fridge, freezer, and microwave oven, along with air conditioning, parking, and internet access. The apartment is close to Tanglewood, Mass MoCA, hiking trails, and a variety of restaurants, offering easy access to cultural and outdoor activities.
Newly Renovated, And Spacious Great For Family - Pittsfield, MA
9.4 96 reviews

Newly Renovated, And Spacious Great For Family

apartment, Pittsfield
This one-bedroom apartment is situated in downtown Pittsfield, just minutes from the Berkshire Museum and the vibrant restaurants and shops of North Street.
The apartment is newly renovated with modern furniture and appliances, including a private parking spot, a jacuzzi, and access control on all doors for added security.
Spacious 2 Bedroom Downtown Very Nice Area! - Pittsfield, MA
9.6 49 reviews

Spacious 2 Bedroom Downtown Very Nice Area!

apartment, Pittsfield
This Pittsfield apartment rental is centrally located, a 5-minute walk from downtown's main street, offering easy access to numerous cafes, restaurants, shops, and a movie theater.
The two-bedroom, one-bathroom unit comfortably sleeps four guests and includes amenities such as air conditioning, internet, and parking.

Choose the Right Family Lodgings in Pittsfield, MA

These family-friendly lodgings in Pittsfield, MA offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.

Marie's Place, Unit 1 - Pittsfield, MA
9.9 119 reviews

Marie's Place, Unit 1

apartment, Pittsfield
This Pittsfield apartment is conveniently located just a 7-minute drive from the Bosquet ski area and 28 minutes from Jiminy Peak, making it ideal for winter sports enthusiasts. The apartment enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 3-bedroom rental can accommodate up to 6 guests and features a spacious eat-in kitchen and living room. Enjoy the enclosed front porch or the small outside deck, relax with the provided wet towel basket, and take advantage of the off-street parking for two cars.
Minutes To Tanglewood With Massive Backyard - Pittsfield, MA
9.8 39 reviews

Minutes To Tanglewood With Massive Backyard

apartment, Richmond
This peaceful countryside retreat is located just outside of Richmond, offering a serene escape from the city while still being close to its attractions. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious house has 5 bedrooms and 2 bathrooms, comfortably accommodating up to 10 guests. Enjoy the fully equipped kitchen, cozy pellet stove, and private garden, perfect for relaxing and enjoying the tranquility of the countryside.
Spacious 4-bedroom Colonial Gem In Downtown Lenox - Pittsfield, MA
9.7 178 reviews

Spacious 4-bedroom Colonial Gem In Downtown Lenox

apartment, Lenox
This Lenox lakefront vacation home, a four-bedroom apartment, is conveniently located within a 15-minute walk of The Bookstore and Lenox Library, and less than 1.2 miles from Ventfort Hall Mansion and Shakespeare & Company.
The 4-bedroom rental boasts a fully equipped kitchen, two bathrooms, in-unit laundry, a terrace, garden, and parking, plus on-site amenities including barbecue grills and a Smart TV, offering serene lake views and proximity to Lenox's cultural attractions.
New Reno Historic Creamery In Berkshires W/hot Tub - Pittsfield, MA
10 5 reviews

New Reno Historic Creamery In Berkshires W/hot Tub

manor house, East Nassau
This New Lebanon vacation home, a short drive from Mount Lebanon Shaker Village and Queechy Lake, offers a convenient location for exploring nearby attractions like Tanglewood Music Center and Hancock Shaker Village.
The 4-bedroom, 3-bathroom property sleeps 9 guests and includes a fully equipped kitchen, in-house laundry, Wi-Fi, air conditioning, a jacuzzi, and a garden; nearby outdoor recreation options include Bousquet Ski Area and Zema's Nursery.

Frequently Asked Questions about accommodations in Pittsfield, MA

  • What are the top attractions and must-see sites in Pittsfield, MA?

    You definitely want to check out the Berkshire Museum, it has a great collection of art and history. The Clark Art Institute is also a must-see, they have an amazing collection of Impressionist and early modern art, and the grounds are beautiful. And don't forget about the Barrington Stage Company, they put on some great shows throughout the year.
  • What are the best accommodations in Pittsfield, MA?

    Among the accommodations in Pittsfield, MA, Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Pittsfield, MA?

    The biggest event is the 10 Days of Summer festival in July, it's a great way to experience local music and art. You should also check out the Pittsfield Farmers Market on Saturdays, it's a great place to get fresh produce and local crafts. And if you're in town during the fall, you can't miss the foliage, it's absolutely stunning.
  • What are the best accommodations with a pool in Pittsfield, MA?

  • What are the most convenient modes of transportation within Pittsfield, MA?

    Pittsfield is pretty walkable, especially downtown. You can also take the bus, the Berkshire Regional Transit Authority has routes throughout the city. If you're planning on exploring the surrounding area, renting a car is your best bet.
  • What are the best accommodations with a jacuzzi in Pittsfield, MA?

  • What outdoor activities and adventures are popular in and around Pittsfield, MA?

    There's plenty to do outdoors in Pittsfield. You can hike or bike the Appalachian Trail, go kayaking on Lake Onota, or visit the nearby Mount Greylock State Reservation, the highest point in Massachusetts. You can also check out the Taconic Crest Trail, which runs along the Taconic Mountains.
  • What are the best accommodations for families and kids in Pittsfield, MA?

    The best accommodations for families and kids in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • What types of accommodations are available in Pittsfield, MA?

    You can find everything from budget-friendly motels to upscale hotels in Pittsfield. There are also a few bed and breakfasts and vacation rentals available. You can also find some great places to stay in the nearby towns of Lenox and Stockbridge.
  • What are the best pet friendly accommodations in Pittsfield, MA?

    The best pet friendly accommodations in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • When is the best time to visit Pittsfield, MA?

    The best time to visit Pittsfield is in the fall, when the leaves change color. It's also a great time to visit in the summer, when the weather is warm and there are lots of outdoor activities to enjoy. You can find some great deals on accommodations during the shoulder seasons, too.
  • What are the best accommodations with parking in Pittsfield, MA?

    Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the best accommodations with parking in Pittsfield, MA.

  • What local dishes and culinary experiences are a must-try in Pittsfield, MA?

    You have to try the Berkshire pork. It's a local specialty, and there are plenty of restaurants in Pittsfield that serve it. You should also check out the local breweries, they're making some really great craft beers. You can also find some great Italian food in Pittsfield, it's a popular cuisine here.
  • In which part of Pittsfield, MA should you consider renting accommodation?

    Downtown Pittsfield is a good choice, it's close to all the action and has a good selection of restaurants and shops. If you're looking for something quieter, you might want to consider staying in the nearby town of Lenox, which is known for its beautiful scenery and charming shops.

Popular destinations

Best Pittsfield, MA accommodation with a kitchen

Your Berkshires Home Base - Pittsfield, MA
9.9 19 reviews

Your Berkshires Home Base

apartment, Dalton
This Dalton, Massachusetts family-friendly apartment rental is conveniently located near Tanglewood and Mass MoCA, offering easy access to Berkshire cultural attractions.
The three-bedroom, two-bathroom dwelling sleeps six, includes a dedicated office, a full kitchen with dishwasher, and provides access to a garden and parking.
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4 - Pittsfield, MA
9.5 9 reviews

Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4

apartment, Hancock
This Hancock apartment, the "Game Night Suite at Jiminy Peak," is conveniently located near Jiminy Peak Ski Resort and 34 miles from Albany International Airport.
The 500-square-foot unit features one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, jacuzzi, and fitness center.
1st Floor Mountain View Suite Ski On/off At Jiminy- Fully Redone Decor - Pittsfield, MA
8.8 8 reviews

1st Floor Mountain View Suite Ski On/off At Jiminy- Fully Redone Decor

apartment, Hancock
This Hancock slopeside condo is located within two miles of Jiminy Peak Mountain Resort, the Alpine Super Slide, and the Mountain Coaster, offering convenient access to area attractions.
This 500-square-foot apartment features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit entertainment, and access to an indoor pool, fitness center, and jacuzzi.
Cantabile Life In The Berkshires - Pittsfield, MA
9.9 217 reviews

Cantabile Life In The Berkshires

apartment, Pittsfield
This apartment is located in a quiet, friendly neighborhood in Pittsfield, just minutes from several lakes, mountains, and attractions like Tanglewood and Bousquet Ski Area. It boasts excellent ratings for location, cleanliness, and user satisfaction.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.

Neighborhoods and points of interest in Pittsfield, MA

Best Pittsfield, MA accommodation with parking

3 Br+ 4level Winter Ski Rental  Looking 4 Seasonal Renter  1 Mile Off Of Jiminey - Pittsfield, MA
9.6 17 reviews

3 Br+ 4level Winter Ski Rental Looking 4 Seasonal Renter 1 Mile Off Of Jiminey

apartment, Lanesborough
This Lanesborough condo is located less than 3 miles from Jiminy Peak Mountain Resort and Mount Greylock State Reservation, offering easy access to skiing, hiking, and scenic mountain views.
This 1750-square-foot vacation rental boasts four bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, in-unit jacuzzi, and access to a shared pool, fitness center, and tennis court.
Cozy Cabin In The Berkshire Resort - Pittsfield, MA
8.2 7 reviews

Cozy Cabin In The Berkshire Resort

cabin, Hancock
This Hancock, Massachusetts mountain home is part of a resort, conveniently located approximately 20 miles from both Tanglewood and the Cranwell Spa & Golf Club.
This 9150-square-foot vacation rental boasts two bedrooms, two bathrooms, and sleeps eight, featuring a fully equipped kitchen, hot tub, private patio, fitness center access, a pool, and a jacuzzi, plus free Wi-Fi and parking.
New Reno Historic Creamery In Berkshires W/hot Tub - Pittsfield, MA
9.4 37 reviews

New Reno Historic Creamery In Berkshires W/hot Tub

gîte, East Nassau
This East Nassau farmhouse rental, situated on a historic 50-acre farm near Tanglewood, offers easy access (within 30 minutes) to four ski resorts, six lakes, the Rockwell Museum, Hancock Shaker Village, and Mount Greylock.
The spacious Creamery suite features four bedrooms, two bathrooms, sleeps nine, and includes a full kitchen, Jacuzzi, and access to 50 acres of walking trails, a fire pit, and BBQ grill.
Berkshire's Family Gathering & Mountain Escape! - Pittsfield, MA
No reviews

Berkshire's Family Gathering & Mountain Escape!

apartment, Cheshire
This four-bedroom, three-bathroom apartment in Cheshire is a 9-minute drive from Mount Greylock State Reservation and a 17-minute drive from Windsor Lake State Park, offering convenient access to nature and cultural attractions like Western Gateway Heritage State Park, 14 minutes away.
This accommodation accommodates up to 12 guests and includes amenities such as Wi-Fi, air conditioning, a dryer, and basic toiletries.

Best Pittsfield, MA lodging with a pool

Among the 288 accommodations in Pittsfield, MA, here are the 4 best ones with a pool

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-ski On/off Country Inn Redone - Pittsfield, MA
10 12 reviews

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-ski On/off Country Inn Redone

apartment, Hancock
Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous - Pittsfield, MA
9.6 34 reviews

Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous

apartment, Hancock
2 Br 2ba Condo Jiminy Peak Retreat W Mtn Views - Pittsfield, MA
9.5 12 reviews

2 Br 2ba Condo Jiminy Peak Retreat W Mtn Views

apartment, Hancock
Wow-new Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn - Pittsfield, MA
9.0 17 reviews

Wow-new Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

apartment, Hancock

Browse 5-Star Accommodations in Pittsfield, MA

Comfort and a prime location define these luxury lodgings in Pittsfield, MA, each hand-selected with your total relaxation in mind.

House W/ View In The Berkshires. - Pittsfield, MA
9.8 8 reviews

House W/ View In The Berkshires.

house, Pittsfield

Top-Rated Pet-Friendly Lodgings in Pittsfield, MA

Traveling with a pet to Pittsfield, MA is effortless when your lodging is equipped with nearby dog parks and city walks right on the doorstep.

Charming Beautiful Apartment In Central Pittsfield - Pittsfield, MA
9.2 82 reviews

Charming Beautiful Apartment In Central Pittsfield

apartment, Pittsfield
Luxurious Family Home- Central Berkshire Location - Pittsfield, MA
10 2 reviews

Luxurious Family Home- Central Berkshire Location

apartment, Richmond
Comfortable Berkshires Retreat On Mtn Resort, Siso - Pittsfield, MA
9.8 47 reviews

Comfortable Berkshires Retreat On Mtn Resort, Siso

apartment, Hancock
Berkshires Sanctuary With Outdoor Living Area & Firepit. 8minutes To Tanglewood! - Pittsfield, MA
10 15 reviews

Berkshires Sanctuary With Outdoor Living Area & Firepit. 8minutes To Tanglewood!

apartment, Richmond
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